Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Sébastien Prévost, Karen Thai, Nina Schützenmeister, Graeme Coulthard, William Erb, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

29 Citations (Scopus)

Abstract

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

Original languageEnglish
Pages (from-to)504-507
Number of pages4
JournalOrganic Letters
Volume17
Issue number3
DOIs
Publication statusPublished - 6 Feb 2015

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